WO2004048395A1 - Compose phosphorescent et element electroluminescent renfermant ce compose - Google Patents

Compose phosphorescent et element electroluminescent renfermant ce compose Download PDF

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WO2004048395A1
WO2004048395A1 PCT/JP2003/014816 JP0314816W WO2004048395A1 WO 2004048395 A1 WO2004048395 A1 WO 2004048395A1 JP 0314816 W JP0314816 W JP 0314816W WO 2004048395 A1 WO2004048395 A1 WO 2004048395A1
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phosphorescent compound
formula
light
electroluminescent
group
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PCT/JP2003/014816
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English (en)
Japanese (ja)
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Satoshi Seo
Hideko Inoue
Atsushi Tokuda
Ryoji Nomura
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Semiconductor Energy Laboratory Co., Ltd.
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Priority to DE60326633T priority Critical patent/DE60326633D1/de
Priority to JP2004554994A priority patent/JP4574358B2/ja
Priority to AU2003302414A priority patent/AU2003302414A1/en
Priority to EP03811907A priority patent/EP1566385B1/fr
Publication of WO2004048395A1 publication Critical patent/WO2004048395A1/fr

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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/92—Ketonic chelates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • the present invention relates to a compound capable of converting a triplet excited state to luminescence (hereinafter, referred to as a “phosphorescent compound”). Further, the present invention includes an anode, a cathode, and a layer containing an organic compound capable of emitting light by applying an electric field (hereinafter, referred to as an “electroluminescent layer”), and the electroluminescent layer is phosphorescent.
  • the present invention relates to an electroluminescent element containing a neutral compound, and a light emitting device using the electroluminescent element.
  • organic compound organic molecule becomes energized (excited) when it absorbs light. Through this excited state, various reactions (photochemical reactions) or luminescence (luminescence) may occur, and various applications have been made.
  • the photochemical reaction there is a reaction (addition of oxygen) of singlet oxygen with an unsaturated organic molecule (for example, see Non-Patent Document 1). Since the ground state of the oxygen molecule is a triplet state, singlet state oxygen (singlet oxygen) is not generated by direct photoexcitation. However, in the presence of other triplet excited molecules, singlet oxygen is generated, which can lead to an oxygen addition reaction. At this time, the compound capable of forming the aforementioned triplet excited molecule is called a photosensitizer.
  • Phosphorescence is light emission caused by transition between energies having different multiplicity.
  • phosphorescence refers to light emission that occurs when returning from a triplet excited state to a singlet ground state (in contrast to the singlet emission). Emission upon returning from the excited state to the singlet ground state is called fluorescence).
  • an electroluminescent element an element which emits light by applying an electric field
  • the light emitting mechanism of the electroluminescent element is a carrier injection type.
  • the electroluminescent layer is usually formed of a thin film having a thickness of less than 1 m.
  • such an electroluminescent device has an electroluminescent layer. Since these are self-luminous elements that emit light, there is no need for a backlight as used in conventional liquid crystal displays. Therefore, it is a great advantage that it can be made extremely thin and lightweight.
  • the time from carrier injection to recombination is about several tens of nanoseconds considering the carrier mobility of the electroluminescent layer. Even in the process from light emission to light emission, light emission occurs on the order of microseconds. Therefore, one of the features is that the response speed is extremely fast.
  • the electroluminescent element is a carrier-injection type light emitting element, it can be driven by a DC voltage and is less likely to generate noise.
  • the driving voltage first, the thickness of the electroluminescent layer should be a uniform ultra-thin film of about 100 nm, and the electrode material should be selected so as to reduce the carrier injection barrier to the electroluminescent layer. ), A sufficient luminance of 100 cd / ni 2 was achieved at 5.5 V (for example, see Non-Patent Document 2).
  • electroluminescent devices Due to such characteristics as thinness and light weight, high-speed response, and low-voltage DC drive, electroluminescent devices are attracting attention as next-generation flat panel display devices. In addition, since it is a self-luminous type and has a wide viewing angle, it has relatively good visibility, and is considered to be effective as an element used for a display screen of a portable device.
  • the light emission observed in such an electroluminescent device is a molecular exciton. Is a light emission phenomenon when returning to the ground state.
  • S * singlet excited state
  • T * triplet excited state
  • the extraction efficiency is said to be about 20%.
  • Non-Patent Document 4 uses a porphyrin complex having platinum as a central metal
  • Non-Patent Document 5 uses an organometallic complex having iridium as a central metal.Each complex introduces a third transition element as a central metal. Phosphorescent compounds. Some of them well exceed the theoretical limit of 5% for the external quantum efficiency mentioned above.
  • the triplet excitation energy generated by the iridium complex can be reduced. It can be moved to DCM2 to contribute to the emission of DCM2 (Non-Patent Document 6).
  • DCM2 emits light from a singlet excited state (fluorescence)
  • the triplet excitation energy of the efficiently generated complex of the complex can be used as the singlet excitation energy of another molecule, DCM2.
  • the iridium complex which is a phosphorescent compound, plays a role similar to that of the above-described photosensitizer, and increases the proportion of the singlet excited state of DCM2.
  • an organic compound that can convert triplet excitation energy into light emission that is, an electroluminescent device using a phosphorescent compound can achieve higher external quantum efficiency than before. And the higher the external quantum efficiency, the higher the emission luminance. Therefore, an electroluminescent device using a phosphorescent compound is expected to occupy a large weight in future development as a method for achieving high luminance emission and high luminous efficiency.
  • phosphorescent compounds are liable to cause intersystem crossing, and Since it is easy to emit light (phosphorescence) from the excited state, it is useful to use it as a photosensitizer or to apply it to an electroluminescent device, and it is a promising compound. is there.
  • the iridium complex used in Non-Patent Documents 5 and 6 is a kind of organometallic complex called an ortho-metal complex. Since this complex has a phosphorescence lifetime of several hundred nanoseconds and a high phosphorescence quantum yield, the decrease in efficiency with an increase in luminance is smaller than that of the porphyrin complex. In this sense, such an orthometal complex using a heavy metal is one guideline for synthesizing phosphorescent compounds.
  • Non-Patent Document 5 The structure of the ligand of the iridium complex described in Non-Patent Document 5 is relatively simple, and emits green light with good color purity.However, in order to change the emission color to another color, the structure of the ligand is required. Need to be changed.
  • Non-Patent Document 7 various ligands and iridium complexes using the ligands have been synthesized, and some luminescent colors have been realized.
  • An object of the present invention is to provide a new phosphorescent compound by synthesizing an orthometal complex using a ligand that is easily synthesized.
  • another object is to provide an electroluminescent element with high luminous efficiency by manufacturing an electroluminescent element using the phosphorescent compound. Further, another object is to provide a light-emitting device with low power consumption by manufacturing a light-emitting device using the electroluminescent element.
  • the present inventor has proposed that a complex represented by the following general formula [Chemical formula 1] synthesized by orthometalation (a kind of cyclomethylation) of a ligand of the general formula [Chemical formula 9] can emit phosphorescence. I found that. Since the ligand represented by the general formula [Chemical formula 9] can be synthesized very easily, this orthometal complex may be synthesized at a low cost in the future.
  • R] L is an alkyl group or ⁇ Li Ichiru group or Ari Le group having a substituent or a heterocyclic residue or a heterocyclic residue having a substituent.
  • R 2 it is Represents hydrogen, an alkyl group, an aryl group, an aryl group having a substituent, a heterocyclic residue, or a heterocyclic residue having a substituent
  • R 3 and R 4 are the same But may be different, hydrogen or halo A hydrogen atom, an alkyl group, an alkoxyl group, an aryl group, an aryl group having a substituent, a heterocyclic residue, or a heterocyclic residue having a substituent.
  • M represents a Group 9 element or a Group 10 element.
  • n 2
  • n 1
  • L is a monoanionic ligand having a beta-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, or a monoanionic bidentate chelate coordinate having a phenolic hydroxyl group. Represents the child, Accordingly, the constitution of the present invention provides a phosphorescent compound represented by the above general formula [Formula 1].
  • the present invention is characterized in that in the general formula [1], the central metal M is iridium or platinum.
  • the ligand L is a monoanionic ligand having a diketone structure, a monoanionic bidentate chelating ligand having a galboxyl group, or a phenolic ligand. Any monoanionic bidentate chelating ligand having a hydroxyl group may be used, but any of the monoanionic ligands represented by the following structural formulas [Formula 2] to [Formula 8] is preferable. These monoanionic chelating ligands are effective because they have high coordination ability and can be obtained at low cost. 11 Therefore, by applying the present invention to an electroluminescent device, the efficiency of the device can be improved, which is very effective. Therefore, the present invention includes an electroluminescent device using the phosphorescent compound of the present invention.
  • the phosphorescent compound of the present invention may be used as a sensitizer as described in Non-Patent Document 6, but it is more preferable to use it as a luminous body as described in Non-Patent Document 5. It is more effective in terms of luminous efficiency. Therefore, the present invention is characterized by an electroluminescent device using the phosphorescent compound of the present invention as a light emitter. Since the thus obtained electroluminescent device of the present invention can realize high luminous efficiency, a light emitting device (image display device or light emitting device) using the same as a light emitting device can realize low power consumption. . Therefore, the present invention includes a light emitting device using the electroluminescent element of the present invention.
  • a light-emitting device in this specification refers to an image display device or a light-emitting device using an electroluminescent element as a light-emitting element.
  • a connector is connected to the electroluminescent element, for example, anisotropic conductive film (ACF) or flexible printed circuit (FPC) or TAB (Tape Automated Bonding) tape or TCP (Tape Carrier Package).
  • ACF anisotropic conductive film
  • FPC flexible printed circuit
  • TAB Tape Automated Bonding tape or TCP (Tape Carrier Package).
  • COG Chip On Glass
  • a new phosphorescent compound can be provided.
  • an electroluminescent element using the phosphorescent compound an electroluminescent element with high emission efficiency can be provided.
  • a light-emitting device and an electric appliance using the electroluminescent element a light-emitting device and an electric appliance with low power consumption can be provided.
  • FIG. 1 is a diagram illustrating an element structure of an electroluminescent element according to Embodiment 1.
  • FIG. 2 is a diagram illustrating an element structure of an electroluminescent element according to Embodiment 2.
  • FIG. 3 is a diagram illustrating an element structure of an electroluminescent element according to Embodiment 3.
  • FIG. 4 illustrates a light-emitting device.
  • FIG. 5 is a diagram illustrating electric appliances.
  • FIG. 6 is a graph showing an absorption 'excitation' emission spectrum of the phosphorescent compound of the present invention.
  • FIG. 7 is a graph showing absorption, excitation, and emission spectra of the phosphorescent compound of the present invention.
  • the ligand represented by the general formula [Chemical formula 9] can be synthesized by the following synthetic scheme [Chemical formula 10].
  • an orthometal complex as the phosphorescent compound of the present invention is formed.
  • a known synthesis method may be used.
  • iridium chloride hydrate is used as the central metal raw material, mixed with the ligand of the general formula [Chemical Formula 9], and placed under a nitrogen atmosphere.
  • a chlorine-bridged binuclear complex is synthesized by refluxing (synthesis scheme [Chem. 11] below).
  • the obtained binuclear complex and the ligand L are mixed and refluxed under a nitrogen atmosphere, whereby the chlorine bridge is cleaved with the ligand L to obtain the phosphorescent compound of the present invention (see below). Synthetic scheme [Formula 1 2]).
  • the method for synthesizing the phosphorescent compound used in the present invention is not limited to the above-described synthesis method.
  • the phosphorescent compound of the present invention thus obtained can obtain various luminescent colors by changing the structure of the ligand represented by the general formula [Chemical Formula 9]. Specific examples thereof include, for example, the following structural formulas [Idani 13] to [Chemical 17]. However, the phosphorescent compound used in the present invention is not limited to these.
  • the phosphorescent compound of the present invention can be used as a photosensitizer ⁇ phosphorescent material. As described below, a mode in which the phosphorescent compound of the present invention is applied to an electroluminescent device will be described below.
  • the electroluminescent device of the present invention basically includes an electroluminescent layer (hole injection layer) containing the above-described phosphorescent compound of the present invention (the above general formula [Chemical Formula 1]) between a pair of electrodes (anode and cathode). , A hole transport layer, a light emitting layer, a blocking layer, an electron transport layer, an electron injection layer, etc.).
  • the material forming the light emitting layer includes not only a material composed of only an organic compound material but also a structure partially including an inorganic compound.
  • the light emitting layer containing the phosphorescent compound of the present invention the hole injection layer, the hole transport layer, the hole blocking layer (hole blocking layer), and the electron transport layer made of a low molecular material are used.
  • the device configuration of the electroluminescent device having the device will be described with reference to FIG.
  • a first electrode 101 is formed on a substrate 100, an electroluminescent layer 102 is formed on the first electrode 101, and a second electrode 101 is formed thereon. Is formed.
  • the material used for the substrate 100 may be any material used for a conventional electroluminescent element, such as glass, quartz, or transparent plastic. What consists of etc. can be used.
  • first electrode 101 in Embodiment 1 functions as an anode
  • second electrode 103 functions as a cathode
  • the first electrode 101 is formed of an anode material.
  • the anode material that can be used here include metals, alloys, and electrically conductive compounds having a large work function (a work function of 4.0 eV or more), and It is preferable to use a mixture, etc.
  • Specific examples of the anode material include IT ⁇ (indium tin oxide), and IZO (indium) obtained by mixing 2 to 20% of zinc oxide (Z ⁇ ) with indium oxide.
  • urn zincoxide gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (C o), copper (Cu), palladium (Pd), or a nitride of a metal material (TiN) can be used.
  • a cathode material used for forming the second electrode 103 a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (a work function of 3.8 eV or less) is preferably used.
  • the cathode material include elements belonging to Group 1 or 2 of the Periodic Rule of the Elements, that is, alkali metals such as Li and Cs, and alkaline earth metals such as Mg, Ca, and Sr.
  • an alloy containing child these Mg: Ag, a 1: L i
  • compound (L i F, C s F , C a F 2) other be formed by transition metals including rare earth metals
  • metals including alloys
  • anode material and cathode material are used for vapor deposition, sputtering, etc.
  • a thinner film By forming a thinner film, a first electrode 101 and a second electrode 103 are formed, respectively.
  • the thickness is preferably 10 to 500 nm.
  • the electroluminescent device of the present invention light generated by recombination of carriers in the electroluminescent layer is emitted outside from one or both of the first electrode 101 and the second electrode 103. That is, when light is emitted from the first electrode 101, the first electrode 101 is formed of a light-transmitting material, and when light is emitted from the second electrode 103 side, the second electrode 101 is formed.
  • the electrode 103 is formed of a translucent material.
  • the electroluminescent layer 102 is formed by stacking a plurality of layers, in Embodiment 1, the hole-injecting layer 111, the hole-transporting layer 112, the light-emitting layer 113, and the hole-blocking layer It is formed by laminating 114 and the electron transport layer 115.
  • a phthalocyanine-based compound As a hole-injecting material for forming the hole-injecting layer 111, a phthalocyanine-based compound is effective.
  • phthalocyanine abbreviated as H 2 —P c
  • copper phthalocyanine abbreviated as ji!-? Ji
  • an aromatic amine-based compound that is, a compound having a benzene ring-nitrogen bond
  • Widely used materials include, for example, 4,4'-bis [N- (3-methylphenyl) -N-phenylamino] -biphenyl (abbreviation: TPD) and its derivatives 4,4 'Bis [N— (1-naphthyl) -1-N-phenylamino] -biphenyl (abbreviation: Hiichi NPD), or 4, 4', 4 "—Tris (N, N-diphenylamino) — Trifenylamine (abbreviation: TDATA), 4, Starburst type aromatic amine compounds such as 4 ', 4 "tris [ ⁇ _ (3-methylphenyl) - ⁇ -phenylamino] monotriphenylamine (abbreviation: MTDATA).
  • TPD 4,4'-bis [N- (3-methylphenyl) -N-phenylamino] -biphenyl
  • MTDATA Trifenylamine
  • the light emission S113 includes the ortho-metal complex represented by the general formula [Formula 1], and is formed by co-evaporation of the ortho-metal complex and a host material.
  • a host material a known material can be used.
  • CBP 4,4′-bis (N-carbazolyl) -biphenyl
  • TPBI 1,3,5-benzene
  • TPBI 1,3,5-benzene
  • Examples of the hole blocking material forming the hole blocking layer 114 include bis (2-methyl-18-quinolinolato) -14-phenylphenolate aluminum (abbreviation: BA lq) and 1,3-bis [5- (p-tert-butylphenyl) — 1,3,4-oxaziazol-1-yl] benzene (abbreviation: OXD-7), 3- (4-tert-butylphenyl) —4-phenyl — 5— (4-Biphenyl) — 1,2,4-triazole (abbreviation: TAZ), 3- (4—tert-butylphenyl) —4-1 (4-ethylphenyl) 1 5— (4—biphenyl Lil) — 1, 2, 4-triazole (abbreviation: pEt TAZ), pasophenanthone phosphorus (abbreviation: BPhen), bathocuproin (abbreviation: BCP), etc. can be used.
  • the electron transporting material for forming the electron transport layer 115 tris (8-quinolinolato) aluminum (abbreviation: Al Q 3 ), tris (5-methyl-8-quinolinolato) aluminum (abbreviation: AlmQ) 3 ), bis (10-hydroxy Shibenzo [h] - quinolinato) beryllium abbreviated or metal complex having a B e B q 2) quinoline skeleton or a base Nzokinorin skeleton such, etc. BA 1 Q described previously are preferred.
  • bis [2- (2-hydroxyphenyl) benzoxazolate] zinc (abbreviation: Zn (BOX) 2 )
  • bis [2- (2-hydroxyphenyl) benzothiazolat] zinc (abbreviation: Zn
  • metal complexes having an oxazole-based or thiazole-based ligand such as BTZ) 2 there are also metal complexes having an oxazole-based or thiazole-based ligand such as BTZ) 2 ).
  • 2- (4-biphenylyl) — 5- (4-tert-butylphenyl) — 1,3,4-oxadiazole (abbreviation: PBD) OXD-7, TAZ, p-Et TAZ, BPhen, BCP, etc. can also be used as the electron transporting material.
  • the light emitting layer 113 containing the phosphorescent compound of the present invention, the hole injection layer 111 made of a low molecular material, the hole transport layer 112, the hole blocking layer (hole blocking layer) 114, An electroluminescent device having the electron transport layer 115 can be formed.
  • the phosphorescent compound of the present invention is used as a guest material in the light-emitting layer 113, and the light-emitting element emits light emitted from the phosphorescent compound of the present invention. is there.
  • Embodiment 2 an element configuration of an electroluminescent element having a light-emitting layer containing the phosphorescent compound of the present invention and a hole-injection layer made of a polymer material and forming these by a wet process will be described. This will be described using 2.
  • the substrate 200, the first electrode 201, and the second electrode 203 Since the same material can be used in the same manner as in Embodiment Mode 1, the description is omitted.
  • the electroluminescent layer 202 is formed by stacking a plurality of layers. In Embodiment 2, the electroluminescent layer 202 is formed by stacking the hole injection layer 211 and the light emitting layer 212. Is done.
  • Examples of the hole injecting material forming the hole injecting layer 211 include polyethylene dioxythiophene (abbreviation: PEDOT) doped with polystyrene sulfonic acid (abbreviation: PSS), and polyaniline. And polyvinyl carbazole (abbreviation: PVK) can be used.
  • PEDOT polyethylene dioxythiophene
  • PSS polystyrene sulfonic acid
  • PVK polyvinyl carbazole
  • the light emitting layer 212 contains the phosphorescent compound of the present invention represented by the general formula [Fig. 1] as a guest material.
  • the host material may be a bipolar material, but may be a bipolar material by mixing a hole transport material and an electron transport material.
  • a hole transporting polymer eg, PVK
  • the above-described electron transporting material eg, PBD
  • a solution is prepared by adding an appropriate amount (about 5 wt%) of the phosphorescent compound of the present invention, and the light emitting layer 212 can be obtained by wet coating the solution.
  • an electroluminescent device having the light emitting layer 212 containing the phosphorescent compound of the present invention and the hole injection layer 211 made of a polymer material and forming these by a wet process. it can.
  • Embodiment 3 a light-emitting layer containing two types of the phosphorescent compound and the fluorescent compound of the present invention, a hole injection layer, a hole transport layer, and a hole blocking layer (e) made of a low molecular material are used.
  • the device configuration of an electroluminescent device having a metal blocking layer and an electron transporting layer will be described with reference to FIG.
  • the substrate 300, the first electrode 301, the second electrode 303, the hole injection layer 311, the hole transport layer 312, the hole blocking layer 314, and the electron transport layer 315 are the same as those in Embodiment 1. Since the same material can be used and formed in a similar manner, the description is omitted.
  • the light-emitting layer 313 of this embodiment includes a host material, a phosphorescent compound of the present invention that is a first guest material, and a fluorescent compound that is a second guest material.
  • a host material the material described in Embodiment 1 may be used.
  • a known fluorescent compound can be used as the second guest material.
  • DCM1, DCM2, DCJTB, quinacridone, N, dimethylquinacridone, rubrene, perylene, DPT, Co— 6, PMDFB, BTX, ABTX. Etc. can be used.
  • the electroluminescent device of Embodiment 3 is a light-emitting device that emits light emitted from a fluorescent compound and emits light, and the luminous efficiency of the fluorescent compound is improved compared to the conventional state. Can be.
  • the phosphorescent compound of the present invention represented by the above structural formula [Formula 13]
  • the synthesis method is exemplified. First, an equimolar amount of 3-thiophenecarpoxyaldehyde and aniline are refluxed in ethanol for 4 hours, and then the solvent is distilled off to obtain a ligand raw material represented by the following structural formula [Chemical Formula 18]. (Yellow liquid).
  • FIG. 6 shows the absorption spectrum, excitation spectrum, and emission spectrum (PL) of the obtained phosphorescent compound (Structural Formula [Chemical Formula 13]) of the present invention.
  • the absorption spectrum of the ligand raw material (structural formula [Chem. 18]) is also shown.
  • the absorption spectrum 2 has a shoulder on the long wavelength side (around 34 Onm and between 35 Onm and 40 Onm) compared to the spectrum ⁇ of the ligand raw material. , which indicates a triplet ⁇ _ ⁇ * transition and a triplet MLCT transition.
  • the position of the excitation spectrum 3 coincides with the position of the triplet excitation, and it is considered that the triplet excited state contributes to light emission.
  • the compound of the present invention is a phosphorescent compound.
  • the light emission spectrum was blue-violet light emission having a peak at about 425 mn.
  • FIG. 7 shows an absorption spectrum, an excitation spectrum, and an emission spectrum (PL) of the obtained phosphorescent compound (Structural Formula [Chemical Formula 15]) of the present invention.
  • the absorption spectrum of the ligand raw material (Structural formula [Chem. 18]) is also shown.
  • the absorption spectrum 2 has two peaks on the long wavelength side (around 340 mn to 37 Onm) compared to the spectrum ⁇ of the ligand raw material, and the triplet C—C * Indicates transitions and triplet ML CT transitions.
  • the position of the excitation vector 3 coincides with the position of the triplet excitation, and it is considered that the triplet excited state contributes to light emission. This indicates that the compound of the present invention is a phosphorescent compound.
  • the light emission spectrum I was blue light emission having a peak at about 45 Onm.
  • FIG. 4A is a top view illustrating the light-emitting device
  • FIG. 4B is a cross-sectional view of FIG. 4A cut along AA ′.
  • Reference numeral 401 indicated by a dotted line denotes a drive circuit unit (source-side drive circuit)
  • 402 denotes a pixel unit
  • 403 denotes a drive circuit unit (gate-side drive circuit).
  • 404 is a sealing substrate
  • 405 is a sealant
  • the inside 407 surrounded by the sealant 405 is a space.
  • Reference numeral 408 denotes wiring for transmitting signals input to the source-side drive circuit 401 and the gate-side drive circuit 403, and a video signal and a clock from an FPC (flexible print circuit) 409 serving as an external input terminal. Receives signals, start signals, reset signals, etc. Although only the FPC is shown here, a printed wiring board (PWB) is attached to this FPC. May be.
  • the light emitting device in this specification includes not only the light emitting device main body but also a state in which the FPC or the PWB is attached thereto. Next, the cross-sectional structure will be described with reference to FIG. A driving circuit portion and a pixel portion are formed over the substrate 410.
  • a source side driving circuit 401 which is a driving circuit portion and a pixel portion 402 are shown.
  • the source side driver circuit 401 is a CMOS circuit formed by combining an n-channel TFT 423 and a p-channel TFT 424.
  • the TFT forming the driving circuit may be formed by a known CMOS circuit, PMOS circuit, or NMOS circuit.
  • a driver integrated with a driver circuit formed on a substrate is shown, but this is not always necessary, and the driver circuit can be formed not on the substrate but outside.
  • the pixel portion 402 is formed by a plurality of pixels including a switching TFT 411, a current control TFT 412, and a first electrode 413 electrically connected to a drain thereof.
  • an insulator 414 is formed to cover an end of the first electrode 413.
  • it is formed by using a positive photosensitive acrylic resin film.
  • a curved surface having a curvature is formed at an upper end or a lower end of the insulator 414.
  • a positive photosensitive acrylic is used as the material of the insulator 414
  • An electroluminescent layer 416 and a second electrode 417 are formed over the first electrode 413.
  • a material used for the first electrode 413 functioning as an anode a material having a large work function is preferably used.
  • single-layer films such as ITO (indium tin oxide) film, indium zinc oxide (IZO) film, titanium nitride film, chromium film, tungsten film, Zn film, Pt film, and titanium nitride film
  • a stacked structure of a film mainly containing aluminum, a three-layer structure of a titanium nitride film, a film mainly containing aluminum, and a titanium nitride film, or the like can be used.
  • the electroluminescent layer 416 is formed by an evaporation method using an evaporation mask or an ink jet method.
  • the phosphorescent compound of the present invention (the above general formula [Chemical formula 1]) is partially used, and other materials that can be used in combination include low molecular weight materials. Or a polymer material.
  • an organic compound is often used as a single layer or a stacked layer.
  • a structure in which an inorganic compound is used as a part of a film made of the organic compound is also included. It shall be.
  • the second electrode (cathode) 417 formed on the electroluminescent layer 416 a material having a small work function (A1, Ag, Li, Ca, or an alloy thereof MgAg, Mg ln, a l L i, C aF 2 or C aN) may be used. Note that when light generated in the electroluminescent layer 416 is transmitted through the second electrode 417, the second electrode (cathode) 417 is formed of a thin film of gold.
  • the lamination of the transparent conductive film ITO (indium oxide-tin oxide alloy), oxidized indicator ⁇ arm oxide-zinc oxide alloy (I n 2 0 3 -Z n O), zinc oxide (Z n O), etc.) Is good.
  • ITO indium oxide-tin oxide alloy
  • oxidized indicator ⁇ arm oxide-zinc oxide alloy I n 2 0 3 -Z n O
  • zinc oxide Z n O
  • the sealing substrate 404 by bonding the sealing substrate 404 to the element substrate 410 with the sealing agent 405, the space 4 surrounded by the element substrate 401, the sealing substrate 404, and the sealing agent 405 is formed.
  • 07 has an electroluminescent element 4 18 provided.
  • the space 407 may be filled with an inert gas (such as nitrogen or argon) or may be filled with a sealant 405.
  • an epoxy resin is preferably used for the sealant 405.
  • these materials do not transmit moisture and oxygen as much as possible.
  • FRP Fiberlass-Reinforced Plastics
  • a plastic substrate made of PVF (polypinyl fluoride), mylar, polyester, acryl, or the like can be used as a material used for the sealing substrate 404.
  • a light emitting device having the electroluminescent element of the present invention can be obtained.
  • Example 1 various electric appliances completed using the light-emitting device having the electroluminescent element of the present invention will be described.
  • Examples of electrical appliances manufactured using the light emitting device having the electroluminescent element of the present invention include a video camera, a digital camera, a goggle type display (head mounted display), a navigation system, and a sound reproducing device (car audio device). , Audio components, etc.), notebook personal computers, game consoles, portable information terminals (mopile computers, mobile phones, portable game consoles, electronic books, etc.), and image playback devices equipped with recording media (specifically, Digital video disc (DVD) or other recording medium, and a device equipped with a display device capable of displaying the image).
  • Fig. 5 shows specific examples of these appliances.
  • FIG. 5 shows specific examples of these appliances.
  • FIG. 5A shows a display device, which includes a housing 200, a support base 200, a display portion 200, a part of speakers 204, a video input terminal 205, and the like. . It is manufactured by using the light emitting device having the electroluminescent element of the present invention for the display portion 203.
  • the display device includes all information display devices for personal computers, TV broadcast reception, advertisement display, and the like.
  • FIG. 5 (B) shows a notebook personal computer, which includes a main body 2201, a housing 222, a display 222, a keypad 220, and an external connection port 220.
  • FIG. 5C shows a mopile computer, which includes a main body 2301, a display portion 2302, a switch 2303, operation keys 2304, an infrared port 2305, and the like. It is manufactured by using the light emitting device having the electroluminescent element of the present invention for the display portion 2302.
  • FIG. 5 (D) shows a portable image reproducing device (specifically, a DVD reproducing device) equipped with a recording medium, which includes a main body 2401, a housing 2402, a display section A2403, Display section B2404, recording medium (DVD, etc.) Reading section2405, operation keys2400
  • a portable image reproducing device specifically, a DVD reproducing device
  • a recording medium which includes a main body 2401, a housing 2402, a display section A2403, Display section B2404, recording medium (DVD, etc.) Reading section2405, operation keys2400
  • Display section A 2 4 0 3 is mainly image information Is displayed, and the display portion B 244 mainly displays character information, and the light emitting device having the electroluminescent element of the present invention is used for these display portions A, B 243, and 244. It is produced by this.
  • the image reproducing device provided with the recording medium includes a home game machine and the like.
  • FIG. 5E shows a goggle-type display (head-mounted display), which includes a main body 2501, a display section 2502, and an arm section 2503. It is manufactured by using the light emitting device having the electroluminescent element of the present invention for the display portion 2502.
  • Fig. 5 (F) shows a video camera, main unit 2601, display unit 2602, 'housing 260, external connection port 2604, remote control receiving unit 2605, Includes an image receiving unit 2606 knottery 260, 0.7, a voice input unit 2608, an operation key 2609, an eyepiece unit 26010, and the like. It is manufactured by using the light emitting device having the electroluminescent element of the present invention for the display portion 2602.
  • Fig. 5 (G) shows a mobile phone, main body 2701, housing 270, display section 270, audio input section 274, audio output section 270 , Operation keys 276, external connection port 277, antenna 278, etc. It is manufactured by using the light emitting device having the electric field light emitting element of the present invention for the display portion 270 3. Note that the display portion 2703 displays white characters on a black background, thereby reducing power consumption of the mobile phone.
  • the applicable range of the light emitting device having the electroluminescent element of the present invention is extremely wide, and this light emitting device can be applied to electric appliances in all fields.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un nouveau composé phosphorescent obtenu par synthèse d'un complexe métallique ortho, avec utilisation de ligands facilement synthétisés. En outre, l'invention concerne un élément électroluminescent, d'un haut rendement de luminescence, utilisant le composé phosphorescent précité. De plus, l'invention concerne un dispositif luminescent à faible consommation d'énergie, utilisant l'élément électroluminescent précité. En particulier, on réalise la synthèse d'un composé phosphorescent de formule générale (1) et l'on forme un élément électroluminescent caractérisé en ce qu'il comprend ledit composé phosphorescent. En vue d'obtenir une émission de phosphorescence d'efficacité accrue du point de vue effet d'atomes lourds, on utilise de préférence un métal lourd comme métal central. Ainsi, le composé phosphorescent est caractérisé en ce que, dans la formule générale (1), le métal central M est l'iridium ou le platine.
PCT/JP2003/014816 2002-11-26 2003-11-20 Compose phosphorescent et element electroluminescent renfermant ce compose WO2004048395A1 (fr)

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DE60326633T DE60326633D1 (de) 2002-11-26 2003-11-20 Phosphoreszenzverbindung und diese enthaltendes elektrolumineszenzelement
JP2004554994A JP4574358B2 (ja) 2002-11-26 2003-11-20 燐光性化合物
AU2003302414A AU2003302414A1 (en) 2002-11-26 2003-11-20 Phosphorescent compound and electroluminescent element including the same
EP03811907A EP1566385B1 (fr) 2002-11-26 2003-11-20 Compose phosphorescent et element electroluminescent renfermant ce compose

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JP2002342647 2002-11-26
JP2002-342647 2002-11-26

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AU2003302414A1 (en) 2004-06-18
CN100352815C (zh) 2007-12-05
US7252895B2 (en) 2007-08-07
EP1566385B1 (fr) 2009-03-11
US20050112400A1 (en) 2005-05-26
DE60326633D1 (de) 2009-04-23
JP4574358B2 (ja) 2010-11-04
US7078114B2 (en) 2006-07-18
EP1566385A1 (fr) 2005-08-24
CN1717411A (zh) 2006-01-04
EP1566385A4 (fr) 2008-02-20
US20060128974A1 (en) 2006-06-15

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